Syntheses of novel delocalized cations and fluorinated anions, new fluorinated solvents and additives for lithium ion batteries

Progress in Solid State Chemistry

Volumn 42, Issue 4, 2014, Pages 202-217

  Bottcher T ^a   Duda, B ^a   Kalinovich, N ^a   Kazakova, O ^a   Ponomarenko, M ^a   Vlasov, K ^a   Winter, M ^b   Roschenthaler G V ^a  

^a JACOBS UNIVERSITY BREMEN   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Delocalized cations; Fluorinated electrolyte salts; Low and high temperature performance; Safety; SEI formation; Solvents and additives

Indexed keywords

ACCIDENT PREVENTION; ADDITIVES; AMIDES; LITHIUM COMPOUNDS; NEGATIVE IONS; POLYELECTROLYTES; POSITIVE IONS; SALTS; SOLVENTS; SULFUR COMPOUNDS;

ELECTROCHEMICAL STABILITIES; ELECTROLYTE ADDITIVES; ELECTROLYTE SALTS; HIGH TEMPERATURE PERFORMANCE; OVERCHARGE PROTECTION; RECHARGEABLE LITHIUM ION BATTERY; RING OPENING REACTION; SEI FORMATIONS;

LITHIUM-ION BATTERIES;

EID: 84920158271     PISSN: 00796786     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progsolidstchem.2014.04.013     Document Type: Review

References (77)

1. S.A. Ullrich, G.L. Gard, R.L. Nafshun, and M.M. Lerner Lithium salts of bis(perfluoroalkyl)sulfonic acids: synthesis, characterization and conductivity studies J Fluor Chem 79 1996 33 38
2. M. Henrich, A. Marhold, A.A. Kolomeitsev, N. Kalinovich, and G.-V. Röschenthaler A new family of delocalized lipophilic cations Tetrahedron Lett 44 2003 5795 5798
3. N. Kalinovich, O. Kazakova, and G.-V. Röschenthaler Delocalized lipophilic cations as a source of naked fluoride and phase-transfer catalysts H.W. Roesky, Efficient preparation of fluorine compounds 2013 Wiley 220 226
4. Y. Ein-Eli, S.R. Thomas, R. Chadha, T.J. Blakley, and V.R. Koch Li-ion battery electrolyte formulated for low-temperature applications J Electrochem Soc 144 1997 823 829
5. K. Xu Nonaqueous liquid electrolytes for lithium-based rechargeable batteries Chem Rev 104 2004 4303 4418
6. M. Winter The solid electrolyte interphase - the most important and the least understood solid electrolyte in rechargeable Li batteries Z Für Phys Chem 223 2009 1395 1406
7. M.R. Wagner, J.H. Albering, K.C. Moeller, J.O. Besenhard, and M. Winter XRD evidence for the electrochemical formation of in PC-based electrolytes Electrochem Commun 7 2005 947 952
8. H. Buqa, A. Würsig, J. Vetter, M.E. Spahr, F. Krumeich, and P. Novák SEI film formation on highly crystalline graphitic materials in lithium-ion batteries J Power Sources 153 2006 385 390
9. S.-K. Jeong, M. Inaba, R. Mogi, Y. Iriyama, T. Abe, and Z. Ogumi Surface film formation on a graphite negative electrode in lithium-ion batteries: atomic force microscopy study on the effects of film-forming additives in propylene carbonate solutions Langmuir 17 2001 8281 8286
10. R. McMillan, H. Slegr, Z.X. Shu, and W. Wang Fluoroethylene carbonate electrolyte and its use in lithium ion batteries with graphite anodes J Power Sources 81-82 1999 20 26
11. H.J. Santner, C. Korepp, M. Winter, J.O. Besenhard, and K.C. Möller In-situ FTIR investigations on the reduction of vinylene electrolyte additives suitable for use in lithium-ion batteries Anal Bioanal Chem 379 2004 266 271
12. K. Abe, H. Yoshitake, T. Kitakura, T. Hattori, H. Wang, and M. Yoshio Additives-containing functional electrolytes for suppressing electrolyte decomposition in lithium-ion batteries Electrochimica Acta 49 2004 4613 4622
13. J.-T. Lee, Y.-W. Lin, and Y.-S. Jan Allyl ethyl carbonate as an additive for lithium-ion battery electrolytes J Power Sources 132 2004 244 248
14. R. Chen, F. Wu, L. Li, Y. Guan, X. Qiu, and S. Chen Butylene sulfite as a film-forming additive to propylene carbonate-based electrolytes for lithium ion batteries J Power Sources 172 2007 395 403
15. H. Ota, T. Akai, H. Namita, S. Yamaguchi, and M. Nomura XAFS and TOF-SIMS analysis of SEI layers on electrodes J Power Sources 119-121 2003 567 571
16. G.H. Wrodnigg, J.O. Besenhard, and M. Winter Ethylene sulfite as electrolyte additive for lithium-ion cells with graphitic anodes J Electrochem Soc 146 1999 470 472
17. G.H. Wrodnigg, J.O. Besenhard, and M. Winter Cyclic and acyclic sulfites: new solvents and electrolyte additives for lithium ion batteries with graphitic anodes? J Power Sources 97-98 2001 592 594
18. G.H. Wrodnigg, T.M. Wrodnigg, J.O. Besenhard, and M. Winter Propylene sulfite as film-forming electrolyte additive in lithium ion batteries Electrochem Commun 1 1999 148 150
19. C. Korepp, W. Kern, E.A. Lanzer, P.R. Raimann, J.O. Besenhard, and M. Yang 4-Bromobenzyl isocyanate versus benzyl isocyanate - New film-forming electrolyte additives and overcharge protection additives for lithium ion batteries J Power Sources 174 2007 637 642
20. C. Korepp, W. Kern, E.A. Lanzer, P.R. Raimann, J.O. Besenhard, and M.H. Yang Isocyanate compounds as electrolyte additives for lithium-ion batteries J Power Sources 174 2007 387 393
21. J.-T. Lee, M.-S. Wu, F.-M. Wang, Y.-W. Lin, M.-Y. Bai, and P.-C.J. Chiang Effects of aromatic esters as propylene carbonate-based electrolyte additives in lithium-ion batteries J Electrochem Soc 152 2005 A1837 A1843
22. Q. Xia, B. Wang, Y.P. Wu, H.J. Luo, S.Y. Zhao, and T. van Ree Phenyl tris-2-methoxydiethoxy silane as an additive to PC-based electrolytes for lithium-ion batteries J Power Sources 180 2008 602 606
23. B. Wang, Q.T. Qu, L.C. Yang, Q. Xia, Y.P. Wu, and D.L. Zhou 2-Phenylimidazole as an additive to prevent the co-intercalation of propylene carbonate in organic electrolyte for lithium-ion batteries J Power Sources 189 2009 757 760
24. C. Korepp, H.J. Santner, T. Fujii, M. Ue, J.O. Besenhard, and K.C. Möller 2-Cyanofuran - a novel vinylene electrolyte additive for PC-based electrolytes in lithium-ion batteries J Power Sources 158 2006 578 582
25. 6-based lithium ion electrolytes Electrochem Solid-State Lett 8 2005 A365 A368
26. A. Sano, and S. Maruyama Decreasing the initial irreversible capacity loss by addition of cyclic sulfate as electrolyte additives J Power Sources 192 2009 714 718
27. B. Wang, H.P. Zhang, L.C. Yang, Q.T. Qu, Y.P. Wu, and C.L. Gan Improving electrochemical performance of graphitic carbon in PC-based electrolytes by using N-vinyl-2-pyrrolidone as an additive Electrochem Commun 10 2008 1571 1574
28. G. Park, H. Nakamura, Y. Lee, and M. Yoshio The important role of additives for improved lithium ion battery safety J Power Sources 189 2009 602 606
29. 4/dioxolane electrolyte J Electrochem Soc 127 1980 2025 2027
30. Boese O, Rieland M, Seffer D, Kalbreyer W. Use of alkoxy esters. Solvay Fluor derivate WO0178183.
31. R. Schmitz, R. Schmitz, R. Müller, O. Kazakova, N. Kalinovich, and G.-V. Röschenthaler Methyl tetrafluoro-2-(methoxy) propionate as co-solvent for propylene carbonate-based electrolytes for lithium-ion batteries J Power Sources 205 2012 408 413
32. Winter M, Röschenthaler G-V, Schmitz R, Kalinovich N, Passerini S, Lex-Balducci A, et al. Electrolytes comprising propylene carbonate for batteries and accumulators. Westfälische Wilhelms-Universität Jacobs University Bremen [WO2012084066].
33. B. Dolenský, J. KvIÍčala, J. Paleček, and O. Paleta Methyl 3,3,3-trifluoropyruvate: an improved procedure starting from hexafluoropropene-1,2-oxide; identification of byproducts J Fluor Chem 115 2002 67 74
34. S.H. Brown, and R.H. Crabtree Making mercury-photosensitized dehydrodimerization into an organic synthetic method. Vapor-pressure selectivity and the behavior of functionalized substrates J Am Chem Soc 111 1989 2935 2946
35. Passerini S, Schmitz R, Schmitz R, Müller R, Schreiner C, Röschenthaler G-V, et al, Lösungsmittel für Elektrolyte. Westfälische Wilhelm-Universität Jacobs University Bremen [DE102012104567.4].
36. Bae SB. Manufacturing method of light immiting diode including current spreading layer. Electronics and Communications Research Institute D [KR1000534692009].
37. Röschenthaler G-V, Kalinovich N, Vlasov K, Schedlbauer T, Kasnatscheew J, Schmitz R, et al. deSEI-bildender Elektrolytzusatz. Jacobs University Bremen [EP2013053949].
38. L. Xiao, X. Ai, Y. Cao, and H. Yang Electrochemical behavior of biphenyl as polymerizable additive for overcharge protection of lithium ion batteries Electrochimica Acta 49 2004 4189 4196
39. S. Tobishima, Y. Ogino, and Y. Watanabe Influence of electrolyte additives on safety and cycle life of rechargeable lithium cells J Appl Electrochem 33 2003 143 150
40. N. Iwayasu, H. Honbou, and T. Horiba Overcharge protection effect and reaction mechanism of cyclohexylbenzene for lithium ion batteries J Power Sources 196 2011 3881 3886
41. H.J. Santner, K.C. Möller, J. Ivančo, M.G. Ramsey, F.P. Netzer, and S. Yamaguchi Acrylic acid nitrile, a film-forming electrolyte component for lithium-ion batteries, which belongs to the family of additives containing vinyl groups J Power Sources 119-121 2003 368 372
42. K.C. Möller, T. Hodal, W.K. Appel, M. Winter, and J.O. Besenhard Fluorinated organic solvents in electrolytes for lithium ion cells J Power Sources 97-98 2001 595 597
43. E. Krämer, R. Schmitz, S. Passerini, M. Winter, and C. Schreiner 1-Fluoropropane-2-one as SEI-forming additive for lithium-ion batteries Electrochem Commun 16 2012 41 43
44. T. Böttcher, O. Shyshkov, M. Bremer, B.S. Bassil, and G.-V. Röschenthaler Carbene complexes of phosphorus(V) fluorides by oxidative addition of 2,2-difluorobis(dialkylamines) to phosphorus(III) halides Organometallics 31 2011 1278 1280
45. Röschenthaler G-V, Böttcher T, Kalinovich N, Winter M, Passerini S, Kunze M, et al. Elektrolyt-Zusatz für Lithium-basierte Energiespeicher. Westfälische Wilhelm-Universität Jacobs University Bremen [DE102011055028].
46. C. Dippel, R. Schmitz, R. Müller, T. Böttcher, M. Kunze, and G.-V. Röschenthaler Carbene adduct as overcharge protecting agent in lithium ion batteries J Electrochem Soc 159 2012 A1587 A1590
47. T. Böttcher, B.S. Bassil, and G.-V. Röschenthaler Complexes of Ge(IV)- and Sn(IV)-fluorides with cyclic and acyclic carbenes: bis(dialkylamino)-difluoromethylenes as carbene sources Inorg Chem 51 2012 763 765
48. 4: a versatile carbene transfer reagent - synthesis from silicochloroform Chem Sci 4 2013 77 83
49. 3N.2HF, a new convenient reagent for nucleophilic fluorine displacement reactions Tetrahedron Lett 31 1990 6527 6530
50. M. Ue Role-assigned electrolytes: additives M. Yoshio, R.J. Brodd, A. Kozawa, Lithium-ion batteries science and technologies 2006 Springer 75 119
51. M. Adachi, K. Tanaka, and K. Sekai Aromatic compounds as redox shuttle additives for 4 V Class secondary lithium batteries J Electrochem Soc 146 1999 1256 1261
52. M. Choy de Martinez, O.P. Márquez, J. Márquez, F. Hahn, B. Beden, and P. Crouigneau In situ spectroscopic investigation of the anodic oxidation of 1,4-dimethoxybenzene at platinum electrodes Synth Met 88 1997 187 196
53. Z. Chen, Q. Wang, and K. Amine Understanding the stability of aromatic redox shuttles for overcharge protection of lithium-ion cells J Electrochem Soc 153 2006 A2215 A2219
54. J.R. Dahn, J. Jiang, L.M. Moshurchak, M.D. Fleischauer, C. Buhrmester, and L.J. Krause High-rate overcharge Protection of LiFePO4-based Li-ion cells using the redox shuttle additive 2,5-ditertbutyl-1,4-dimethoxybenzene J Electrochem Soc 152 2005 A1283 A1289
55. L.M. Moshurchak, W.M. Lamanna, M. Bulinski, R.L. Wang, R.R. Garsuch, and J. Jiang High-potential redox shuttle for use in lithium-ion batteries J Electrochem Soc 156 2009 A309 A312
56. L. Zhang, Z. Zhang, H. Wu, and K. Amine Novel redox shuttle additive for high-voltage cathode materials Energy Environ Sci 4 2011 2858 2862
57. C. Buhrmester, L.M. Moshurchak, R.L. Wang, and J.R. Dahn The use of 2,2,6,6-tetramethylpiperinyl-oxides and derivatives for redox shuttle additives in Li-ion cells J Electrochem Soc 153 2006 A1800 A1804
58. L.M. Moshurchak, C. Buhrmester, and J.R. Dahn Triphenylamines as a class of redox shuttle molecules for the overcharge protection of lithium-ion cells J Electrochem Soc 155 2008 A129 A131
59. C. Buhrmester, L. Moshurchak, R.L. Wang, and J.R. Dahn Phenothiazine molecules: possible redox shuttle additives for chemical overcharge and overdischarge protection for lithium-ion batteries J Electrochem Soc 153 2006 A288 A294
60. Z. Chen, J. Liu, A.N. Jansen, G. GirishKumar, B. Casteel, and K. Amine Lithium borate cluster salts as redox shuttles for overcharge protection of lithium-ion cells Electrochem Solid-State Lett 13 2010 A39 A42
61. A. Kütt, V. Movchun, T. Rodima, T. Dansauer, G.-V. Röschenthaler, and I. Leito Pentakis(trifluoromethyl)phenyl, a sterically crowded and electron-withdrawing group: synthesis and acidity of pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline J Org Chem 73 2008 2607 2620
62. B.B. Hallac, O.E. Geiculescu, R.V. Rajagopal, S.E. Creager, and D.D. DesMarteau Lithium-conducting ionic melt electrolytes from polyether-functionalized fluorosulfonimide anions Electrochim Acta 53 2008 5985 5991
63. Blakeney A, Dimov O, Ferreira L, Hatfield J, Kocab J, Spaziano J. Photoacid generators for use in photoresist compositions. US2002.
64. Feiring A, Harmer M, Junk C, Schadt F, Schnepp Z. Hydrofluoroalkanesulfonic acids from fluorovinyl ethers. US2006.
65. F. Toulgoat, B.R. Langlois, M. Médebielle, and J.-Y. Sanchez An efficient preparation of new sulfonyl fluorides and lithium sulfonates J Org Chem 72 2007 9046 9052
66. Winter M, Schreiner C, Lex-Balducci A, Müller R, Schmitz R, Röschenthaler G-V, et al. Lithium-2-methoxy-1,1,2,2-tetrafluoro-ethanesulfonate and use thereof as conductive salt in lithium-based energy accumulators. Westfälische Wilhelms-Universität W, Jacobs University Bremen [DE102011052156].
67. T.J. Huang, Z.X. Dong, and J.M. Shreeve 1,1,2,2-Tetrafluoro-2-(polyfluoroalkoxy)ethanesulfonyl fluorides Inorg Chem 26 1987 2604 2606
68. Montanari V, Navarrini W, Staccione AM. Process for preparing perfluoroalkoxysulphonic compounds. EU1996.
69. Winter M, Schreiner C, Lex-Balducci A, Müller R, Schmitz R, Röschenthaler G-V, et al. Conductive salt for lithium-based energy accumulators. Westfälische Wilhelm-Universität Jacobs University Bremen [EP2013053949].
70. D.V. Sevenard, O.G. Khomutov, N.S. Boltachova, V.I. Filyakova, V. Vogel, and G.-V. Röschenthaler Metal and boron derivatives of fluorinated cyclic 1,3-dicarbonyl compounds Z für Naturforsch 64b 2009 541 550
71. I. Krossing, and A. Reisinger Chemistry with weakly-coordinating fluorinated alkoxyaluminate anions: gas phase cations in condensed phases? Coord Chem Rev 250 2006 2721 2744
72. I. Krossing, and I. Raabe Noncoordinating anions - fact or fiction? A survey of likely candidates Angew Chem Int Ed 43 2004 2066 2090
73. 5Li and its reactions with cyclic imines and lactims: synthesis of α-pentafluoroethyl proline J Fluor Chem 129 2008 390 396
74. M.H. Königsmann, E. Lork, I.L. Odinets, V.G. Nenajdenko, N.E. Shevchenko, and G.-V. Röschenthaler α-Pentafluoroethylated amines: a new synthetic approach Mendeleev Commun 16 2006 141 143
75. Barten J, Kadyrov A, Kolomeitsev AA, Marhold A, Röschenthaler G-V, Schneider M. Process for preparing polyfluoroalkyllithium compounds. Bayer AG [US20030065135].
76. O. Kazakova, and G.-V. Röschenthaler Pentafluoroethyl lithium: reactions with carbonyl compounds and epoxides H.W. Roesky, Efficient preparation of fluorine compounds 2013 Wiley 205 209
77. D.P. Graham, and V. Weinmayr Fluoride ion initiated reactions of perfluoro α-olefins. II. The condensation of tetrafluoro-ethylene with perfluoro ketones to yield perfluoro tertiary alcohols J Org Chem 31 1966 957 958